Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

Huifeng Yue; Lin Guo; Shao-Chi Lee; Xiangqian Liu; Magnus Rueping

doi:10.1002/anie.201612624

Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

Huifeng Yue, Lin Guo, Shao-Chi Lee, Xiangqian Liu, Magnus Rueping

Research output: Contribution to journal › Article › peer-review

143 Scopus citations

Abstract

An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.

Original language	English (US)
Pages (from-to)	3972-3976
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	56
Issue number	14
DOIs	https://doi.org/10.1002/anie.201612624 https://doi.org/10.1002/ange.201612624
State	Published - Mar 21 2017

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title = "Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation",

abstract = "An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.",

author = "Huifeng Yue and Lin Guo and Shao-Chi Lee and Xiangqian Liu and Magnus Rueping",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: H.Y. and L.G. acknowledge the China Scholarship Council. Support by King Abdullah University of Science and Technology (KAUST) is gratefully acknowledged.",

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T1 - Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

AU - Yue, Huifeng

AU - Guo, Lin

AU - Lee, Shao-Chi

AU - Liu, Xiangqian

AU - Rueping, Magnus

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: H.Y. and L.G. acknowledge the China Scholarship Council. Support by King Abdullah University of Science and Technology (KAUST) is gratefully acknowledged.

PY - 2017/3/21

Y1 - 2017/3/21

N2 - An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.

AB - An inexpensive nickel(II) catalyst and a hydrosilane were used for the efficient reductive defunctionalization of aryl and heteroaryl esters through a decarbonylative pathway. This versatile method could be used for the removal of ester and amide functional groups from various organic molecules. Moreover, a scale-up experiment and a synthetic application based on the use of a removable carboxylic acid directing group highlight the usefulness of this reaction.

UR - http://hdl.handle.net/10754/623907

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JO - Angewandte Chemie International Edition

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IS - 14

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Selective Reductive Removal of Ester and Amide Groups from Arenes and Heteroarenes through Nickel-Catalyzed C−O and C−N Bond Activation

Abstract

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